Hydrochloric Acid → HCID 89536827, compound

HRID 1774098Notes

Reaction equation

HRID 1774098 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]([NH:5][C:6]1[C:11](Br)=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=1[Br:14])=[O:4].C([Li])CCC.[CH3:22][S:23]SC.Cl>C(OCC)C.CCCCCC>[F:1][C:2]([F:16])([F:15])[C:3]([NH:5][C:6]1[C:11]([S:23][CH3:22])=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=1[Br:14])=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12232Dimethyl DisulfideHCID 64593411HCID 64593411, compoundHCID 178418339Butyllithium

Product 1

HCID 89536827HCID 89536827, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

Under an atmosphere of argon, 69.3 g (95% by weight pure, 182 mmol) of N-(trifluoroacetyl)-2,6-dibromo-4-methylaniline in 900 ml of dry diethyl ether were cooled to a temperature of −70° C. At this temperature, 153 ml of a 2.5M solution (382.5 mmol) of n-butyllithium in hexane were added dropwise. The mixture was subsequently stirred at this temperature for another 30 minutes. At this temperature, a solution of 51.5 g (547 mmol) of dimethyl disulfide in 100 ml of dry diethyl ether was then added dropwise. The contents were stirred at this temperature for 1 h and then at RT for 3 h and subsequently poured into 1000 ml of 1M hydrochloric acid. After phase separation, the aqueous phase was extracted with diethyl ether, the combined organic phases were dried and the filtrate was freed of the solvents. The residue was stirred with heptane for 30 minutes and then filtered. 46.6 g of N-(trifluoroacetyl)-2-bromo-4-methyl-6-(methylthio)aniline were obtained as residue.

Workup

  1. stirringThe contents were stirred at this temperature for 1 h
  2. waitat RT for 3 h
  3. customAfter phase separation
  4. extractionthe aqueous phase was extracted with diethyl ether
  5. customthe combined organic phases were dried
  6. stirringThe residue was stirred with heptane for 30 minutes
  7. filtrationfiltered

Sources & evidence

ORD record
ord-64ad43f2982b4d8da4d36725ba82bebc
Source dataset
uspto-grants-2016_02
Patent number
US09259001B2

Reaction notes

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